Acridine compound

Abstract

A compound represented by formula [I]:wherein R12, R13, R14, R15, and R16 are the same or different and are each hydrogen, halogen, C1-6 alkyl optionally substituted with halogen, or C1-6 alkoxy optionally substituted with halogen; R21, R22, and R23 are the same or different and are each hydrogen, halogen, C1-6 alkyl optionally substituted with halogen, C1-6 alkoxy optionally substituted with halogen, sulfanyl optionally substituted with halogen, nitro, or cyano; R3 is C1-6 alkyl or the like; and X− is an anion.

1 . A compound represented by formula [I]: 
       
         
           
           
               
               
           
         
       
       wherein
 R 12 , R 13 , R 14 , R 15 , and R 16  are the same or different and are each hydrogen, halogen, C 1-6  alkyl optionally substituted with halogen, or C 1-6  alkoxy optionally substituted with halogen; 
 R 21 , R 22 , and R 23  are the same or different and are each hydrogen, halogen, C 1-6  alkyl optionally substituted with halogen, C 1-6  alkoxy optionally substituted with halogen, sulfanyl optionally substituted with halogen, nitro, or cyano; 
 R 3  is C 1-6  alkyl or 
 
       
         
           
           
               
               
           
         
       
       wherein R 32 , R 33 , R 34 , R 35 , and R 36  are the same or different and are each hydrogen, halogen, C 1-6  alkyl optionally substituted with halogen, C 1-6  alkoxy optionally substituted with halogen, sulfanyl optionally substituted with halogen, nitro, or cyano; and
 X −  is an anion; 
 provided that the following cases are excluded: 
 1) all of R 12 , R 13 , R 14 , R 15 , R 16 , R 21 , R 22 , and R 23  are hydrogen, and R 3  is methyl or phenyl; 
 2) all of R 12 , R 14 , R 16 , and R 3  are methyl, and R 23  is hydrogen or fluorine; and 
 3) R 12  is hydrogen or methyl, R 13  is hydrogen or methyl, R 14  is hydrogen or methyl, R 15  is hydrogen or methyl, R 16  is hydrogen or methyl, R 3  is methyl or unsubstituted phenyl, and R 23  is hydrogen. 
 
     
     
         2 . The compound according to  claim 1 , wherein
 R 12 , R 13 , R 14 , R 15 , and R 16  are the same or different and are each hydrogen, fluorine, chlorine, methyl, t-butyl, trifluoromethyl, or trifluoromethoxy;   R 21 , R 22 , and R 23  are the same or different and are each hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, pentafluorosulfanyl, nitro, or cyano; and   R 3  is methyl or   
       
         
           
           
               
               
           
         
       
       wherein R 32 , R 33 , R 34 , R 35 , and R 36  are the same or different and are each hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, pentafluorosulfanyl, nitro, or cyano. 
     
     
         3 . The compound according to  claim 1 , wherein
 R 12 , R 13 , R 14 , R 15 , and R 16  are the same or different and are each hydrogen, fluorine, methyl, t-butyl, trifluoromethyl, or trifluoromethoxy;   R 21  and R 22  are hydrogen, R 23  is fluorine; and   R 3  is methyl or 4-fluorophenyl.   
     
     
         4 . The compound according to  claim 1  selected from the following: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         5 . The compound according to  claim 1 , wherein X is perchlorate ion (ClO 4   − ), hexafluorophosphate ion (PF 6   − ), or tetrafluoroborate ion (BF 4   − ). 
     
     
         6 . A photoredox catalyst selected from the compound according to  claim 1 . 
     
     
         7 . Use of the compound according to  claim 1  as a photoredox catalyst. 
     
     
         8 . A method for producing phenol from optionally substituted benzene, comprising irradiating optionally substituted benzene with visible light in the presence of the compound according to  claim 1 .